Apple's pitch on iPhone 3G is that it's as well suited to enterprise use as a BlackBerry. The core technology is certainly there, with an ActiveSync (Microsoft Exchange Server) mail client, AJAX-capable browser, Cisco-compatible VPN, and Office and PDF mail attachment viewers. iPhone's UI revolutionized the mobile industry with scalable text and graphics, a display surface capable of responding to multifinger gestures, and an on-screen keyboard that works without a stylus.

So iPhone has the essential enterprise ingredients. The question is, does Apple's recipe fit the enterprise better than alternatives? Having worked with iPhone since last June, the honest answer is yes and no. iPhone is an unqualified hit among users. No one will complain about being migrated from whatever they're carrying now to an iPhone 3G. Employees and contractors will trample each other for a shot at an iPhone, unwittingly exposing themselves to better reachability and collaboration. For Mac users, it's practically pointless to carry anything else.

iPhone is a smart way to keep workers in touch while they're traveling because it's an unparalleled lifestyle accessory. Anyone who owns one will always have it with them, talking, texting, surfing, listening to music, and watching videos. Enterprises shouldn't brush this aside as a consideration. A mobile device is of limited use if its user can't wait to be without it.

Apple invested the bulk of its initial effort in the design and implementation of iPhone to make the device irresistible to users. Mission accomplished. Phase two made the device an easy sell to developers. I'm still waiting for phase three, which makes iPhone enterprise-friendly for configuration, equipping, deployment, and management in substantial numbers. Right now, the best I can say is that an enterprise deployment of iPhone can be done, but not as easily, flexibly, or securely as for a BlackBerry or Windows Mobile device.

iBall and iChain

The first barrier to iPhone fleet deployment is the inescapable necessity of iTunes. An online music store client that communicates opaquely with offsite servers is not likely to be part of your standard desktop and notebook build. It's not going to be IT's first choice as a central device configuration terminal. Yet either the user or IT must run iTunes to activate each phone, a tedious interactive process. Only iTunes can be used to back up, restore, or update the firmware or install custom applications on an iPhone. Apple issues iPhone firmware updates frequently. They are effectively mandatory, and each firmware update requires updates to iTunes and the iPhone SDK as well.

If you come from the BlackBerry or Windows Mobile world, activation is a foreign idea. These devices can deploy without ever touching a desktop. The closest they come to activation is enrollment with a mail or collaboration server. User applications can be shipped over the air and installed directly on the device. Firmware updates are few, and I have yet to see one classified as mandatory.

Another barrier to iPhone fleet deployment relates to custom applications that are common in enterprises. From a consumer or individual perspective, the iPhone SDK makes all things possible. From an enterprise perspective, iPhone just doesn't play well with others. It is not possible to port, without completely rewriting, any mobile application you're currently using, with the only exception being HTTP hosted apps with browser front ends.

iPhone has no J2ME or Flash implementation, nor does it support background processes that, for example, maintain connections with middleware for application-specific push, presence, or notification. Apple announced plans to host a notification service to address some of these issues, but it never materialized. Even with that, the most any developer could hope for is that an external notification would trigger an application into the foreground, which a user might find disruptive. Because applications have no access to the iPhone's status bar (which comes and goes in any case), there's no way to indicate a pending or missed communication.

Rules and regs

There is more, too, such as Apple's prohibition of the use of TCP ports under 1000, and the device's inability to operate as a USB storage device. Only iTunes can access iPhone files, and it only allows the transfer of media and applications. Data can be bundled with an application developed in-house, and through that application one could transfer arbitrary data to and from the device. But iPhone imposes strict rules on data such that only the app that created the data may access it. iPhone's browser can neither upload nor download data. In fact, the easiest way to get data in and out of iPhone is through the mail client. E-mail attachments cannot be archived or moved to another iPhone application. They can only be viewed from inside Mail.

With its functional limitations and unusually large management overhead, iPhone is less than a shoo-in for fleet deployment, a scenario for which BlackBerry is specifically designed, and to which Symbian, Palm, and Windows Mobile adapt fairly well with the proper tools.

I do see hope on the horizon. Apple's iPhone Configuration Utility has the makings of an enterprise iPhone pain reliever. It presently includes the ability to present the utility as a Web site from which users and admins can download XML configuration profiles that define common VPN and e-mail settings. This hints at future over-the-air centralized management. I hope that it is Apple's aim to eventually push iTunes out of the enterprise. As for the lack of background processes, Flash and Java, these aren't technical limitations; they are strategic choices. Apple will only revisit these restrictions if it feels they're a barrier to greater iPhone sales.

iPhone is, by design, a device for individuals. But if one of your people brings an iPhone in the door and can be trusted to manage it, it should be welcomed. Likewise, if all your enterprise will ever need from a mobile device is what iPhone delivers out of the box, then none of the issues I've described should dissuade you from distributing a stack of Apple handsets. As I said, nothing could make users happier. But for now, iPhone in the enterprise does not conform to the maxim "the more, the merrier."